How to drink responsibly so you can still be a social butterfly and pay the rent.

By Sarah Moore

As we wind our way toward winter, the temptation to retreat indoors and hibernate can seem irresistible. However, Portland’s many bars and restaurants, beacons of warmth and energy in the blue velvet dark, can invigorate you with actual human interaction and hard liquor. Here is our guide to socializing on a shoestring.

The Monday Antidote

Everyone knows Mondays are hard. The appropriate way to celebrate the death of the worst day of the week is with glass in hand. Luckily, there’s help.

East End dwellers can grab a stool at Roustabout’s expansive bar in the former Nissen Bakery Building on Washington Avenue for off-price libations. The Italian-American restaurant recently introduced a list of enticing wines for under $25 per bottle, available from 4 p.m. to close every Monday. Sip on a bottle of Petit Verdot from Chile for only $16 as you watch the daylight fade through the enormous plate-glass windows. “We like to keep the list seasonal, so the selection will change. But you can expect around eight wines to choose from, all for under $25. It’s a great way to liven up a Monday evening,” says owner Kit Paschal.

On the West End, Bonobo also champions the Monday night out. “We’ve had our half-price Mondays for several years now,” says owner Denise. “It’s a real favorite for locals.” Order up half-price wine, beer, and well drinks from 4 p.m. to close every Monday night. While Roustabout is all cool minimalism, Bonobo is cozy and unflashy. The exposed brick work, tucked-away tables, and large wood-fired oven will ward off the November chill while enticing you with the smell of baking pizza.

Tex-Mex Tuesday

A wine-only diet can come with some lifestyle risks. Thankfully, many Portland eateries are offering delicious meal deals in addition to cut-price beverages. If you can find a seat at Tomaso’s diminutive bar on Hampshire Street on a Tuesday night, then be sure to treat yourself to their Taco Tuesday deal. The space is invariably hopping with a young, noisy crowd of locals and service-industry folk, nursing beers elbow-to-elbow. Expect such unusual delights as cheeseburger jalapeno and Shepherd’s Pie tacos, liberally sprinkled with cheese. It may not be Michelin star, but for only $3 for two tacos and $2 16-ounce Tecate cans, you’ll be sitting pretty for only $5.

Wednesday in the wild west

In years of yore, most Portlanders labeled Wharf Street as a cobbled hellscape of tourists and bachelorette parties, dutifully avoiding its bars until the arrival of fall. The time has come to cast our collective snobbery aside and embrace the unique charms of this section of the Old Port.

Bonfire Country Bar peddles an uproarious pseudo-Southern vibe, complete with rustic decor and blaring country music, seven days a week. Head down for some midweek relief and enjoy $2 drafts chased by $1 house whiskey from 4 to 7 p.m every day. Before long, the alcohol will have you craving the crispy, greasy, and somewhat sweet bacon like never before. Lucky for you, it’s free and unlimited. “I’ve never actually seen someone eat more than two servings, to be honest,” says the barmaid, dressed in the standard uniform of plaid shirt and Daisy Dukes. “It’s pretty salty stuff!” Health risks aside, Bonfire is some light relief in a city full of studiously stylish and understated bars. After all, this is the only place in town you can relax with cheap beer and free food while reclining in a Western saddle.

Thursdays are thirsty

With only one more work day standing between you and the weekend, Thursday nights can extend further into the witching hours. Settle yourself into the warm hubbub of The Corner Room & Grill on the corner of Exchange Street to enjoy their long-standing and often overlooked happy hour deal. House wines, Prosecco, and a rotating draught beer are all only $3 from 4 to 6 p.m. Even better, you can pair your apéritif with a selection of free small-plate snacks delivered fresh from the kitchen.

If you’re not ready to go home once the last crumb has been devoured, make the short walk to Rosie’s on Fore Street–the place where happy hour never ends (at least until close at 1 a.m.)–for $1.50 pints of Miller High Life and free baskets of buttery popcorn.

Friday night Alights

There’s nothing quite like the feeling of elation as you leave work on a Friday afternoon, the weekend stretching uninterrupted before you. Prolong the euphoria by making your way to the petite, purple sanctuary of the Hot Suppa dining room on Congress Street. Many happy-hour deals only run until Thursday, but Hot Suppa has got you covered from 4 to 6 p.m. on Friday nights. Settle into a cozy wooden booth and enjoy $1 off all drinks and $1 half-shell Maine oysters served with fresh horseradish cocktail sauce and lemon. Enjoy the feeling of decadence as you devour the briny feast while sipping on a flavourful glass of kombucha from Urban Farm Fermentory. You’ll leave fully satisfied and with your wallet only marginally lighter. Not bad for a Friday night on the town.

Serving up Saturday

A Saturday afternoon outing to one of Portland’s many breweries is a reliable way to while away an autumn day. Why not visit the first bastion of Portland brewing, Shipyard Brewing Co. on Newbury Street, for a turn in their tasting room? During the fall, Shipyard’s seasonal “Pumpkinhead Ale” frequently infuses the East End with the fragrant, yeasty smell of hops–bringing to mind the aroma of baking muffins. The tasting room is open from 11 a.m. to 6 p.m. every Saturday, and while you may have to wait for your turn at the beer taps, once you’re there a knowledgeable bartender will serve small pours of the brewery’s classic, seasonal, and even unreleased pilot brews with surprising generosity. Best of all? It’s totally free.

Sunday sessions

As the end of the weekend closes in, you may feel like it’s time to give your liver a rest. A trip to Boda on Congress will assuage your Sunday blues, while the delights of the half-price late-night menu will make the thought of a sober evening all the more appealing. Securing a table at Boda during this hallowed weekly period from 9:30 p.m. to 12.45 a.m. is practically a contact sport, but if you’re successful you’ll be duly rewarded. Appetizers such as the Thai peanuts, homemade lobster chips, and the Kanom-Krok quail eggs are devilishly delicious options that don’t exceed $3.50. Indulgence never felt so good on your bank account.